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Method for preparing terbinafine hydrochloride Z-shaped isomer

A technology of terbinafine hydrochloride and terbinafine, which is applied in the field of medicine, can solve the problems of undocumented impurity analysis, detection and the like, and achieve the effects of stable product quality, mild preparation conditions and simple synthesis steps

Active Publication Date: 2015-06-24
吉林修正药业新药开发有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] There are many patent documents about the preparation of terbinafine hydrochloride, all of which describe the preparation process of terbinafine hydrochloride in detail, but there is no record about the analysis and detection of impurities, so as to realize the control of drug quality

Method used

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  • Method for preparing terbinafine hydrochloride Z-shaped isomer
  • Method for preparing terbinafine hydrochloride Z-shaped isomer
  • Method for preparing terbinafine hydrochloride Z-shaped isomer

Examples

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Embodiment Construction

[0018] Weigh 50.0 g of terbinafine EZ mixture into a 500 ml three-necked flask, add 200 ml of isopropanol to it, raise the temperature to 70° C., and keep it warm for 2 hours. Slowly lower the temperature to 20 degrees Celsius and keep it for 2 hours, then lower the temperature to 0 degrees Celsius and keep it for 2 hours. After filtration, the filtrate was concentrated under reduced pressure to obtain an oil.

[0019] Put 10g of oil in a 100ml three-necked flask, add 50ml of 4-chlorophenyl tert-butyl ether, increase the temperature to 120°C, and keep it warm for 1 hour. Then, the temperature was lowered to 10°C, kept for 3 hours, and filtered to obtain a white compound, terbinafine hydrochloride Z isomer. 1 H-NMR (400MHz, CDCl 3 )δ1.25(s, 9H), 2.27(d, 2H), 3.03(d, 2H), 4.06(d, 2H), 5.62(t, 1H), 6.21(t, 1H), 7.10(m, 1H) ), 7.19(m, 1H), 7.29(m, 1H), 7.31(m, 1H), 7.51(m, 1H), 7.64(m, 1H), 7.77(m, 1H)

[0020] Use octadecyl silane-bonded silica gel as a filler (150mm×3.0mm, 5μm, or ...

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Abstract

The invention discloses a method for preparing a terbinafine hydrochloride Z-shaped isomer serving as a high-purity isomer impurity compound for allylamine medicament terbinafine hydrochloride impurity analysis. The preparation method comprises the following steps: 1, adding a terbinafine EZ mixture to isopropanol, heating to 40-86 DEG C for dissolving, preserving the heat for 0.5-4 hours, slowly cooling to 10-20 DEG C, preserving the heat for 1-3 hours, cooling to -10-0 DEG C, preserving the heat for 1-5 hours, filtering, and concentrating the filtrate under reduced pressure to obtain an oily matter; and 2, adding 4-chlorphenyl-tert-butyl ether into the oily matter obtained in step 1, heating to 100-150 DEG C, preserving the heat for 1-5 hours, cooling to 0-40 DEG C, preserving the heat for 1-10 hours, and filtering to obtain an off-white compound. The method has the positive effect of obtaining the terbinafine hydrochloride isomer with relatively high purity. The isomer serving as a known impurity is used in quality analysis of terbinafine hydrochloride to determine the position of an impurity in a sample and survey the resolution between the impurity and the sample, so that the analysis method is more accurate. The preparation conditions are mild, the synthesis steps are simple, and the quality of the product is stable.

Description

Technical field: [0001] The invention belongs to the field of medicine, and specifically relates to an allylamine drug terbinafine hydrochloride isomer impurities with broad-spectrum antifungal activity, (Z)-N-(6,6-dimethylhept-2-ene-4- Alkynyl)-N-methyl-1-naphthylmethylamine preparation method. Background technique: [0002] Terbinafine hydrochloride is an allylamine drug with broad-spectrum antifungal activity. This product can specifically interfere with the early biosynthesis of fungal ergosterol, highly selectively inhibit fungal squalene epoxidase, and block the squalene epoxidation reaction during the formation of fungal cell membranes, thereby achieving killing or Inhibit the effect of fungi. [0003] At present, the main route of administration is still oral preparations, so it is very important to control the purity of drugs. The structure of terbinafine hydrochloride is E configuration, and its Z configuration isomer has low biological activity, but the two configurat...

Claims

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Application Information

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IPC IPC(8): C07C211/30C07C209/88
Inventor 阎君林子琦白冰王化录曹翠
Owner 吉林修正药业新药开发有限公司
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